64190-70-1

Basic information

• Product Name: FMRF AMIDE
• Synonyms: MOLLUSCAN CARDIOEXCITATORY NEUROPEPTIDE;MOLLUSCAN CARDIOEXCITATORY NEUROPEPTIDE 1 1/2 ACOH 2H2O;MOLLUSCAN CARDIOEXCITATORY PEPTIDE;PHE-MET-ARG-PHE AMIDE;PHE-MET-ARG-PHE-NH2;PHE-MET-ARG-PHE-NH2 1/2ACOH 2H2O;FMRF AMIDE;FMRF-AMIDE 1 1/2ACOH 2H2O
• CAS NO: 64190-70-1
• Molecular Formula: C₂₉H₄₂N₈O₄S
• Molecular Weight: 598.76
• Mol File: 64190-70-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.32 g/cm³
• Refractive Index: 1.639
• Storage Temp.: −20°C
• PKA: 13.35±0.46(Predicted)
• CAS DataBase Reference: FMRF AMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: FMRF AMIDE(64190-70-1)
• EPA Substance Registry System: FMRF AMIDE(64190-70-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 64190-70-1(Hazardous Substances Data)

Usage

Description

FMRFamide (FMRFa) was originally isolated as a cardioacceleratory peptide from mollusks. To date, a number of biologically active FMRFas and their related peptides have been identified.

Biological functions

Target cells and function The predominant effect of FaRPs is the reduction of spontaneous muscle contractions, such as in the intestinal muscle and the heart rate. Among FaRP subtypes, some FaRPs function in gut contraction and other subtypes do not.?Physiological discrimination according to different?subtype of FaRPs results in extensive functions.For example, FaRPs exert acceleratory effects on the heart rate, inhibitory effects on gut motility, and modulate synaptic activity. Furthermore, sequential ecdysis behavior is also regulated by FaRPs, consequently activating the downstream of the eclosion hormone (EH) and ecdysistriggering hormone (ETH).During ecdysis, FaRP-expressing Tv neurons are activated by ETH.

Synthesis

Gene, mRNA, and precursor D. melanogaster FMRFa mRNA produces a deduced prepropeptide composed of 347 aa. The prepropeptide is composed of a signal sequence, and 10 copies of FMRFa and extended FaRPs. The mature peptides are processed proteolytically and amidated at each C-terminal of the peptides.

InChI:InChI=1/C29H42N8O4S/c1-42-16-14-23(35-26(39)21(30)17-19-9-4-2-5-10-19)28(41)36-22(13-8-15-34-29(32)33)27(40)37-24(25(31)38)18-20-11-6-3-7-12-20/h2-7,9-12,21-24H,8,13-18,30H2,1H3,(H2,31,38)(H,35,39)(H,36,41)(H,37,40)(H4,32,33,34)/t21-,22-,23-,24-/m0/s1

Upstream product

• 5241-58-7 L-Phenylalanine amide 
• 123197-18-2 H-Phe-Met-Arg-OH 
• 123197-28-4 Boc-Phe-Met-Arg(Mts)-Phe-NH₂ 
• 85642-22-4 N-benzoxycarbonyl-L-phenylalanyl-L-methionyl-N-^γ-nitro-L-arginyl-L-phenylalaninamide 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 13726-76-6 t-butyloxycarbonyl-L-arginine 
• 2188-18-3 Boc-Arg(NO₂)-OH 
• 85642-21-3 N^α-tert-butoxycarbonyl-N^γ-nitro-L-arginyl-L-phenylalaninamide 
• 85651-85-0 N-tert-butoxycarbonyl-L-methionyl-N^γ-nitro-L-arginyl-L-phenylalaninamide 
• 58810-06-3 H-Arg(Mts)-OH 
• 16948-13-3 Boc-Met-OTcp 
• 123197-26-2 Boc-Met-Arg(Mts)-OH 
• 123197-27-3 Boc-Phe-Met-Arg(Mts)-OH 

Relevant articles and documents

Novel Modified Carboxy Terminal Fragments of Neutropeptide Y with High Affinity for Y2-Type Receptors and Potent Functional Antagonism at a Y1-Type Receptor

Peptide analogs of neuropeptide Y (NPY) with a Tyr-32 and Leu-34 replacement resulted in the decapeptide TyrIleAsnLeuIleTyrArgLeuArgTyr-NH2 (9; Table 1) and a 3700-fold improvement in affinity at Y2 (rat brain; IC50 = 8.2 +/- 3 nM) receptors when compared to the native NPY(27-36) C-terminal fragment.In addition, compound 9 was an agonist at Y1 (human erythroleukemia (HEL) cell; ED50 = 8.8 +/- 0.5 nM) receptors with potency comparable to that of NPY(1-36) (ED50 = 5 nM).Molecular dynamics and 1H-NMR were used to propose a solution structure of decapeptide 9 and for subsequent analog design.The replacement of Leu with Pro at position 4 of decapeptide 9 afforded an antagonist of NPY in HEL cells (18, TyrIleAsnProIleTyrArgLeuArgTyr-NH2; IC50 = 100 +/- 5 nM).Deletion of the N-terminal tyrosine of 18 resulted in a 10-fold improvement in antagonistic activity with a parallel 4-fold decrease in Y2 affinity.This potent antagonist may provide further insight into the physiological role(s) for NPY in the mammalian and peripheral nervous system.

SYNTHESIS OF FEMARFAM

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